Iodine → 2-Iodo-3-(4-methoxyphenoxy)benzo[b]thiophene

HRID 1386985

Reaction equation

HRID 1386985 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[S:11][CH:12]=2)=[CH:5][CH:4]=1.[Li]CCCC.[I:24]I>C1COCC1>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[S:11][C:12]=2[I:24])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 807IodineHCID 108249753-(4-Methoxyphenoxy)benzo[b]thiopheneHCID 178418339Butyllithium

Product 1

HCID 106912792-Iodo-3-(4-methoxyphenoxy)benzo[b]thiophene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 133 mg (0.52 mmol) of 3-(4-methoxyphenoxy)benzo[b]thiophene (Part A) in 3 mL of THF was treated with 0.33 mL of 1.6 M n-BuLi in hexanes (0.54 mmol) at −78° C. for 15 min and then treated with 138 mg (0.54 mmol) of I2 in 3 mL of THF. The reaction was allowed to gradually warm to room temperature and then partitioned between brine and EtOAc/hexanes. The two phases were separated, the organic phase was washed with H2O, dried over Na2SO4, and concentrated in vacuo. The residue was crystallized from hexanes to afford 143 mg (0.37 mmol; 72%) of the title compound as a solid.

Workup

  1. custompartitioned between brine and EtOAc/hexanes
  2. customThe two phases were separated
  3. washthe organic phase was washed with H2O
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized from hexanes

Sources & evidence

ORD record
ord-e24f8b5bbe76440ea6c3491bd4deaad9
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Linked notes

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